Nitromethane → 4-Trifluoromethoxy-(2-nitro-vinyl)-benzene

HRID 216102

반응식

HRID 216102 반응식
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.[N+:14]([CH3:17])([O-:16])=[O:15].C([O-])(=O)C.[NH4+]>C(O)(=O)C.O>[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[CH:17][N+:14]([O-:16])=[O:15])=[CH:6][CH:5]=1

참가 물질

6

반응물 3

HCID 6375NitromethaneHCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 517165Ammonium Acetate

생성물 1

HCID 6882334-Trifluoromethoxy-(2-nitro-vinyl)-benzene수율 100.3%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

반응 조건

온도
150 °C

실험 절차

A solution of (4-trifluoromethoxy benzaldehyde (1 g, 5.26 mmol) and nitromethane (0.96 g, 15.8 mmol) in acetic acid (10.6 mL) is treated with ammonium acetate (1.01 g, 13.2 mmol) is heated under microwave to 150° C. for 15 minutes. The reaction mixture is diluted with water, and extracted three times with DCM (50 mL). The combined extracts are washed sequentially with 2 N sodium hydroxide, water, and brine, dried over sodium sulfate and concentrated. The residue is subjected to silica gel chromatography to yield 4-trifluoromethoxy-(2-nitro-vinyl)-benzene (1.23 g) as a solid. A portion of 4-trifluoromethoxy-(2-nitro-vinyl)-benzene (0.504 g, 2.16 mmol) is hydrogenated with hydrogen in a balloon, 10% Pd/C (115 mg, 5 mol %) in MeOH (22 mL) containing concentrated hydrochloric acid (0.27 mL) at room temperature for 15 hours. The mixture is filtered and filtrate is concentrated to a solid that is washed with diethyl ether to obtain 2-(4-trifluoromethoxy-phenyl)-ethylamine hydrochloride [0.3 g, 57%, Intermediate (12)] as a solid. LC/MS: MS: 206 (M+H).

후처리

  1. extractionextracted three times with DCM (50 mL)
  2. washThe combined extracts are washed sequentially with 2 N sodium hydroxide, water, and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f14661b45db5408dbb99328ef303b063
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193183B2

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